Curator’s statement
I’m a Charleston native and lifelong local who has been exploring this city for as long as I can remember. I grew up here and have spent decades wandering downtown streets, trying new restaurants, and showing visiting friends and family around. Charleston isn’t just a place I recommend—it’s home. Over the years, I’ve become the person people call when they’re planning a trip here, helping friends and clients plan everything from where to stay and what to eat to the experiences that truly make a visit memorable. This itinerary reflects the way I personally love to show people Charleston, filled with some of my favorite spots around the city. My goal is to help you experience Charleston in a way that feels thoughtful, relaxed, and memorable, like visiting with a local friend. And hopefully, it will have you planning your next trip before you even leave!
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Day 1: Explore downtown Charleston and go shopping

Spend the day walking through the historic district, exploring colorful streets, and shopping along King Street.
Breakfast: Start the morning with biscuits at Callie’s Hot Little Biscuit. It’s a Charleston classic and the perfect way to start your trip. The cinnamon biscuits are to die for!
Morning activity: Take a walking tour of historic Charleston. It’s one of the best ways to learn about the city’s history, architecture, and hidden alleyways while getting a lay of the land. I always recommend doing this at the beginning of a trip. You can easily DIY it or go with a certified guide.
Lunch: Head to Basic Kitchen for a healthy, vegetable-forward lunch. I always get the Basic Bowl filled with chickpeas and sweet potatoes or their “Good Burger,” a veggie burger that’s surprisingly good. And don’t skip the beet margarita.
Afternoon: Spend the afternoon shopping on King Street. This is Charleston’s main shopping district with everything from local boutiques to national brands. Some of my favorite stops are Lake Pajamas, Croghan's Jewel Box, Under the Almond Trees for kids, Sézane, Beau & Ro, M. Dumas & Sons, Old Whaling Company, Hart Jewelry, and IBU Movement.
Dinner: For dinner, grab a table at 167 Raw for some of the best seafood in the city.

A note from Lindsey
Pro tip: Make a reservation at Bar 167 for drinks first, then go put your name down at 167 Raw since there will likely be a wait.
Day 2: History, relaxation & sunset views

Day two blends Charleston’s historic plantations with a little relaxation and great food.
Breakfast: Enjoy breakfast at your hotel or grab something light before heading out for the morning.
Morning activity: Visit Middleton Place, one of Charleston’s most historic plantations. Walk the gardens, tour the house museum, and learn about the property’s history.
Lunch: Stop by Leon’s Oyster Shop for fried chicken, oysters, and frozen rosé or gin and tonics. If the weather is nice, I definitely recommend sitting outside. I usually order some local oysters, the Siam salad, and a fried oyster sandwich with a frozen rosé.
Afternoon: Book spa appointments for a relaxing afternoon after your morning exploring. The spa at The Dewberry Charleston is one of my absolute favorites and a must if you’re staying there.
Sunset drinks: Head to the rooftop at The Citrus Club for sunset cocktails and beautiful views over the city. It’s one of the highest rooftops in Charleston, so the views are incredible.
Dinner: End the evening with dinner at Merci, a cozy neighborhood restaurant known for its seasonal menu.
Day 3: A local’s perspective

Spend your final day exploring Charleston the way locals do.
Breakfast: Grab a smoothie, juice, or coffee from Huriyali.
Morning activity: Then take a walk through Hampton Park. It’s one of the most beautiful parks in the city and a favorite spot for locals. I love taking morning walks here, and if you visit in March, the azaleas are gorgeous and fill the park with shades of pink!
Brunch/lunch: Right around the corner, have brunch at Park & Grove. It’s a bright café known for its healthy brunch menu and great coffee. It’s the perfect spot for a casual brunch and workout clothes are totally acceptable.
Afternoon/evening activity: Take a boat cruise in Charleston Harbor to spot dolphins or catch sunset, depending on the timing of your trip.
Dinner: Make reservations at Vern’s for dinner. It’s easily my favorite restaurant in Charleston with a creative menu and relaxed atmosphere. They were recently awarded one Michelin star, which is such a big deal for Charleston. Don’t miss the sourdough pita bread, fresh pasta, and the tuna tartare.
After-dinner drinks: End the trip with a nightcap at The Seahorse, which is right around the corner. They make a great martini and the atmosphere is so fun!
Need to know
Make restaurant reservations early, especially if there’s somewhere specific you want to eat! Charleston’s best restaurants book up quickly, particularly on weekends and during busy travel seasons.
Plan to walk a lot while exploring downtown, so comfortable shoes are a must. The historic district is very walkable, and wandering the streets is truly one of the best ways to experience the city.

Travel Advisor
Lindsey Calhoun

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